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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2859-o2860
https://doi.org/10.1107/S1600536810041231

4-Hy­dr­oxy-3-[(4-hy­dr­oxy-6,7-di­methyl-2-oxo-2H-chromen-3-yl)(4-oxo-4H-chromen-3-yl)meth­yl]-6,7-di­methyl-2H-chromen-2-one

Mohammad Asad,a Chuan-Wei Oo,a‡ Hasnah Osman,a Chin Sing Yeapb§ and Hoong-Kun Funb*

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 5 October 2010; accepted 13 October 2010; online 20 October 2010)

In the title compound, C32H24O8, the mol­ecular structure is disordered over two positions with refined site occupancies of 0.8746 (10) and 0.1254 (10). The mean plane of the three chromeno rings make dihedral angles with each other of 65.12 (4), 62.91 (4) and 59.70 (4)° in the major occupancy component and 59.1 (3), 66.1 (3) and 58.8 (3)° in the minor component. Intra­molecular O—H⋯O hydrogen bonds stabil­ize the mol­ecular structure and the crystal structure is stabilized by weak C–H⋯π and π–π inter­actions [centroid–centroid distances 3.496 (6)–3.672 (7) Å].

Related literature

For general background and the biological activity of chromone heterocycle derivatives, see: Waring (1979[Waring, A. J. (1979). In Comprehensive Organic Chemistry, edited by D. H. R. Barton & W. D. Ollis, Vol. 1, p. 1057. Oxford: Pergamon Press.]); Dewick (1994[Dewick, P. M. (1994). In The Flavonoids: Advances in Research since 1986, edited by J. B. Harborne, p. 117. New York: Chapman and Hall.]); Rich (1990[Rich, D. H. (1990). In Comprehensive Medicinal Chemistry, edited by C. Hansch, P. G. Sammes& J. B. Taylor, p. 6. New York: Pergamon Press.]); Masami et al. (2007[Masami, K., Toru, T., Hiroyuki, K., Satoru, T., Hideki, N. & Hiroshi, S. (2007). In Vivo, 21, 829-834.]); Khan et al. (2010[Khan, K. M., Ambreen, N., Mughal, U. R., Jalil, S., Perveen, S. & Choudhary, M. I. (2010). Eur. J. Med. Chem. 45, 4058-4064.]); Nawrot-Modranka et al. (2006[Nawrot-Modranka, J., Nawrot, E. & Graczyk, J. (2006). Eur. J. Med. Chem. 41, 1301-1309.]); Ellis et al. (1978[Ellis, G. P., Becket, G. J. P., Shaw, D., Wilson, H. K., Vardey, C. J. & Skidmore, I. F. (1978). J. Med. Chem. 21, 1120-1126.]); Raj et al. (2010[Raj, T., Bhatia, R. K., Kapur, A., Sharma, M., Saxena, A. K. & Ishar, M. P. S. (2010). Eur. J. Med. Chem. 45, 790-794.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C32H24O8

  • Mr = 536.51

  • Monoclinic, P 21 /c

  • a = 13.6418 (12) Å

  • b = 10.5878 (9) Å

  • c = 21.2316 (15) Å

  • β = 123.480 (4)°

  • V = 2557.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.56 × 0.30 × 0.28 mm
Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.973

  • 37636 measured reflections

  • 10128 independent reflections

  • 7464 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.141

  • S = 1.03

  • 10128 reflections

  • 524 parameters

  • 1102 restraints

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C2–C7 and C2A–C7A benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5A⋯O7 0.82 1.83 2.6464 (19) 174
O6—H6B⋯O4 0.82 1.80 2.6141 (18) 172
C3—H3A⋯Cg1i 0.93 2.91 3.7691 (16) 155
C32—H32B⋯Cg2ii 0.96 2.70 3.499 (3) 140
C29A—H29D⋯Cg3iii 0.96 2.91 3.591 (15) 128
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041231/rz2499sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041231/rz2499Isup2.hkl

checkCIF report


Comment top

The oxygen-containing chromone heterocycles are ubiquitous in plants (Waring, 1979). They form basic nucleus of flavones (Dewick, 1994) and have been found in many biologically active molecules with a broad range of applications in the pharmaceutical industry (Rich, 1990). These derivatives are an important class of compounds, possessing a large number of pharmacological activities such as anti-HIV (Masami et al., 2007), potentially anti-inflammatory (Khan et al., 2010), antibacterial (Nawrot-Modranka et al., 2006), antiallergic (Ellis et al., 1978) and anticancer (Raj et al., 2010) activities.

The molecular structure of the title compound is disordered over two positions (Fig. 1) with refined site occupancies of 0.8746 (10) and 0.1254 (10). The mean plane of the three chromeno rings make dihedral angles of 65.12 (4), 62.91 (4) and 59.70 (4)° for major component and 59.1 (3), 66.1 (3) and 58.8 (3)° for minor component with each other. Intramolecular O5—H5A···O7 and O6—H6B···O4 hydrogen bonds (Table 1) stabilize the molecular structure and generate S(8) ring motifs (Fig. 2). The molecules are stacked down the b axis (Fig. 3) and stabilized by weak C–H···π and π···π interactions [Cg4···Cg5iv of 3.496 (6) Å and Cg5···Cg6v of 3.672 (7) Å; (iv) 1 - x, -1/2 + y, 3/2 - z; (v) 1 - x, 1/2 + y, 3/2 - z. Cg4, Cg5 and Cg6 are centroids of O2A–C18A–C13A–C12A–C11A–C19A, O3A–C21A–C20A–C28A–C27A–C22A and C13A–C18A ring, respectively].

Related literature top

For general background and the biological activity of chromone heterocycle derivatives, see: Waring (1979); Dewick (1994); Rich (1990); Masami et al. (2007); Khan et al. (2010); Nawrot-Modranka et al. (2006); Ellis et al. (1978); Raj et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 6,7-dimethyl-4-hydroxycoumarin (1.05 mmol, 200 mg) and 3-formyl chromone (0.52 mmol, 91 mg) was prepared in ethanol (10 ml) and acetic acid (0.5 ml) was added to it. The reaction mixture was refluxed on water bath for 6 h. The completion of the reaction was monitored by TLC. After completion of the reaction, the crystalline solid was filtered, washed with ethanol and purified by recrystallization from chloroform-methanol mixture to give the pure title compound in 75% yield.

Refinement top

The molecular structure is disordered over two positions with refined site occupancies of 0.8746 (10) and 0.1254 (10). The minor component was refined isotropically. The same Uij parameters were used for the atoms C5A/C31A/C32A. All disordered atoms were subjected to rigid bond and similarity restraints. One of the chromeno ring was restrained to be planar. H10A hydrogen atom was located in a difference Fourier map and refined using a riding model. The rest of hydrogen atoms were positioned geometrically [O–H = 0.82 Å; C–H = 0.93–0.96 Å] and refined using a riding model [Uiso(H) = 1.5Ueq(O); Uiso(H) = 1.2–1.5Ueq(C)]. A rotating-group model was applied for methyl groups.

Structure description top

The oxygen-containing chromone heterocycles are ubiquitous in plants (Waring, 1979). They form basic nucleus of flavones (Dewick, 1994) and have been found in many biologically active molecules with a broad range of applications in the pharmaceutical industry (Rich, 1990). These derivatives are an important class of compounds, possessing a large number of pharmacological activities such as anti-HIV (Masami et al., 2007), potentially anti-inflammatory (Khan et al., 2010), antibacterial (Nawrot-Modranka et al., 2006), antiallergic (Ellis et al., 1978) and anticancer (Raj et al., 2010) activities.

The molecular structure of the title compound is disordered over two positions (Fig. 1) with refined site occupancies of 0.8746 (10) and 0.1254 (10). The mean plane of the three chromeno rings make dihedral angles of 65.12 (4), 62.91 (4) and 59.70 (4)° for major component and 59.1 (3), 66.1 (3) and 58.8 (3)° for minor component with each other. Intramolecular O5—H5A···O7 and O6—H6B···O4 hydrogen bonds (Table 1) stabilize the molecular structure and generate S(8) ring motifs (Fig. 2). The molecules are stacked down the b axis (Fig. 3) and stabilized by weak C–H···π and π···π interactions [Cg4···Cg5iv of 3.496 (6) Å and Cg5···Cg6v of 3.672 (7) Å; (iv) 1 - x, -1/2 + y, 3/2 - z; (v) 1 - x, 1/2 + y, 3/2 - z. Cg4, Cg5 and Cg6 are centroids of O2A–C18A–C13A–C12A–C11A–C19A, O3A–C21A–C20A–C28A–C27A–C22A and C13A–C18A ring, respectively].

For general background and the biological activity of chromone heterocycle derivatives, see: Waring (1979); Dewick (1994); Rich (1990); Masami et al. (2007); Khan et al. (2010); Nawrot-Modranka et al. (2006); Ellis et al. (1978); Raj et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing major (solid-bond) and minor (open-bond) disorder components.
[Figure 2] Fig. 2. The major component of molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The crystal packing of the title compound viewed down the b axis. Only the major component of disorder is shown.
4-Hydroxy-3-[(4-hydroxy-6,7-dimethyl-2-oxo-2H-chromen-3-yl)(4-oxo- 4H-chromen-3-yl)methyl]-6,7-dimethyl-2H-chromen-2-one top
Crystal data top
C32H24O8F(000) = 1120
Mr = 536.51Dx = 1.393 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9464 reflections
a = 13.6418 (12) Åθ = 3.2–33.7°
b = 10.5878 (9) ŵ = 0.10 mm−1
c = 21.2316 (15) ÅT = 100 K
β = 123.480 (4)°Block, colourless
V = 2557.8 (4) Å30.56 × 0.30 × 0.28 mm
Z = 4
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		10128 independent reflections
Radiation source: fine-focus sealed tube7464 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 33.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −21→21
Tmin = 0.946, Tmax = 0.973k = −12→16
37636 measured reflectionsl = −33→31
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.7344P]
where P = (Fo2 + 2Fc2)/3
10128 reflections(Δ/σ)max = 0.001
524 parametersΔρmax = 0.37 e Å−3
1102 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C32H24O8V = 2557.8 (4) Å3
Mr = 536.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.6418 (12) ŵ = 0.10 mm−1
b = 10.5878 (9) ÅT = 100 K
c = 21.2316 (15) Å0.56 × 0.30 × 0.28 mm
β = 123.480 (4)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		10128 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		7464 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.973Rint = 0.037
37636 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511102 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.03Δρmax = 0.37 e Å−3
10128 reflectionsΔρmin = −0.22 e Å−3
524 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C100.59934 (8)0.98504 (9)0.78627 (5)0.02251 (17)
H10A0.64451.05620.81670.027*
O10.73539 (7)0.68760 (8)0.76785 (4)0.02341 (16)0.8746 (10)
O20.47327 (9)1.01052 (8)0.90437 (5)0.02818 (18)0.8746 (10)
O30.37210 (7)1.12802 (8)0.59633 (5)0.02604 (17)0.8746 (10)
O40.55778 (7)0.76495 (7)0.69426 (4)0.02260 (15)0.8746 (10)
O50.82100 (10)0.95360 (11)0.93221 (5)0.0371 (2)0.8746 (10)
H5A0.76280.98650.92740.056*0.8746 (10)
O60.38782 (10)0.81531 (9)0.71296 (5)0.02352 (17)0.8746 (10)
H6B0.44530.80320.71080.035*0.8746 (10)
O70.64315 (8)1.06877 (9)0.92532 (5)0.03188 (19)0.8746 (10)
O80.71448 (9)1.01343 (10)0.70554 (6)0.0333 (2)0.8746 (10)
C10.65408 (11)0.77741 (12)0.75365 (6)0.0200 (2)0.8746 (10)
C20.84098 (10)0.68293 (11)0.83692 (6)0.0238 (2)0.8746 (10)
C30.91643 (11)0.58524 (12)0.84766 (8)0.0300 (2)0.8746 (10)
H3A0.89650.52890.80870.036*0.8746 (10)
C41.02195 (12)0.57262 (15)0.91709 (10)0.0328 (3)0.8746 (10)
C51.05388 (13)0.6590 (2)0.97607 (9)0.0355 (4)0.8746 (10)
C60.97653 (11)0.75649 (15)0.96287 (7)0.0334 (3)0.8746 (10)
H6A0.99670.81431.00120.040*0.8746 (10)
C70.86887 (10)0.76993 (14)0.89335 (7)0.0252 (2)0.8746 (10)
C80.78733 (10)0.87052 (12)0.87659 (6)0.0255 (2)0.8746 (10)
C90.68462 (9)0.87684 (10)0.80711 (6)0.02114 (19)0.8746 (10)
C110.51591 (10)0.96109 (10)0.81050 (6)0.02201 (19)0.8746 (10)
C120.41935 (10)0.88413 (10)0.77386 (6)0.02157 (19)0.8746 (10)
C130.33957 (12)0.87755 (13)0.79841 (9)0.0235 (2)0.8746 (10)
C140.23512 (12)0.80865 (12)0.76169 (7)0.0297 (2)0.8746 (10)
H14A0.21510.76010.71970.036*0.8746 (10)
C150.16077 (16)0.81163 (16)0.78707 (10)0.0369 (3)0.8746 (10)
C160.19036 (18)0.8865 (2)0.84998 (13)0.0388 (4)0.8746 (10)
C170.29428 (13)0.95199 (13)0.88778 (8)0.0351 (3)0.8746 (10)
H17A0.31480.99960.93020.042*0.8746 (10)
C180.36863 (11)0.94693 (11)0.86242 (7)0.0273 (2)0.8746 (10)
C190.54895 (12)1.01699 (11)0.88165 (6)0.0250 (2)0.8746 (10)
C200.54055 (12)1.03192 (10)0.70468 (6)0.02065 (19)0.8746 (10)
C210.42855 (12)1.07318 (11)0.66505 (6)0.0229 (2)0.8746 (10)
H21A0.38621.06290.68710.027*0.8746 (10)
C220.43328 (11)1.14560 (10)0.56314 (7)0.0232 (2)0.8746 (10)
C230.37170 (12)1.20468 (12)0.49245 (7)0.0284 (2)0.8746 (10)
H23A0.29431.23070.47050.034*0.8746 (10)
C240.42912 (16)1.22319 (12)0.45629 (7)0.0309 (3)0.8746 (10)
H24A0.38941.26120.40890.037*0.8746 (10)
C250.54523 (15)1.18597 (13)0.48947 (8)0.0331 (3)0.8746 (10)
H25A0.58281.19990.46450.040*0.8746 (10)
C260.60504 (12)1.12824 (12)0.55951 (8)0.0293 (2)0.8746 (10)
H26A0.68281.10350.58160.035*0.8746 (10)
C270.54863 (12)1.10686 (11)0.59737 (7)0.0231 (2)0.8746 (10)
C280.61095 (10)1.04642 (10)0.67235 (6)0.0235 (2)0.8746 (10)
C291.10440 (15)0.46606 (17)0.92871 (12)0.0492 (4)0.8746 (10)
H29A1.07130.41870.88270.074*0.8746 (10)
H29B1.11530.41150.96820.074*0.8746 (10)
H29C1.17890.50040.94250.074*0.8746 (10)
C301.16883 (12)0.6490 (2)1.05083 (9)0.0493 (4)0.8746 (10)
H30A1.17360.71411.08390.074*0.8746 (10)
H30B1.23210.65861.04380.074*0.8746 (10)
H30C1.17440.56781.07270.074*0.8746 (10)
C310.05114 (17)0.7292 (2)0.74713 (11)0.0545 (5)0.8746 (10)
H31A0.04340.69050.70370.082*0.8746 (10)
H31B−0.01680.78040.73140.082*0.8746 (10)
H31C0.05760.66490.78110.082*0.8746 (10)
C320.1078 (2)0.8923 (2)0.87623 (14)0.0566 (5)0.8746 (10)
H32A0.13890.94900.91840.085*0.8746 (10)
H32B0.09960.80950.89130.085*0.8746 (10)
H32C0.03230.92200.83580.085*0.8746 (10)
O1A0.8805 (6)0.8897 (6)0.9690 (4)0.0415 (16)*0.1254 (10)
O2A0.3213 (6)0.7840 (7)0.7070 (4)0.0353 (14)*0.1254 (10)
O3A0.6758 (6)1.0511 (7)0.6468 (4)0.0364 (15)*0.1254 (10)
O4A0.7459 (7)1.0309 (8)0.9456 (5)0.051 (2)*0.1254 (10)
O5A0.6824 (6)0.7439 (7)0.7564 (3)0.0205 (14)*0.1254 (10)
H5AA0.64380.68550.75740.031*0.1254 (10)
O6A0.5112 (8)1.0139 (7)0.8896 (4)0.0353 (17)*0.1254 (10)
H6AB0.58121.01610.90520.053*0.1254 (10)
O7A0.4578 (5)0.7878 (6)0.6821 (3)0.0300 (13)*0.1254 (10)
O8A0.3923 (7)1.1013 (8)0.6664 (4)0.0350 (17)*0.1254 (10)
C1A0.7792 (9)0.9484 (9)0.9212 (6)0.041 (3)*0.1254 (10)
C2A0.9176 (7)0.7844 (7)0.9466 (5)0.0329 (18)*0.1254 (10)
C3A1.0253 (8)0.7332 (9)1.0020 (6)0.042 (2)*0.1254 (10)
H3AA1.06890.76751.05030.050*0.1254 (10)
C4A1.0660 (12)0.6290 (12)0.9831 (8)0.060 (6)*0.1254 (10)
C5A1.0016 (12)0.5766 (13)0.9100 (9)0.069 (3)*0.1254 (10)
C6A0.8923 (7)0.6330 (8)0.8564 (5)0.0255 (15)*0.1254 (10)
H6AA0.84690.60010.80780.031*0.1254 (10)
C7A0.8538 (6)0.7333 (7)0.8751 (4)0.0176 (16)*0.1254 (10)
C8A0.7432 (6)0.7985 (7)0.8234 (4)0.0295 (16)*0.1254 (10)
C9A0.7094 (7)0.8993 (7)0.8435 (5)0.0287 (16)*0.1254 (10)
C11A0.4883 (8)0.9182 (9)0.7822 (5)0.0289 (16)*0.1254 (10)
C12A0.4555 (8)0.9462 (10)0.8290 (5)0.0382 (19)*0.1254 (10)
C13A0.3474 (8)0.9000 (10)0.8161 (6)0.023 (2)*0.1254 (10)
C14A0.2988 (10)0.9292 (12)0.8567 (7)0.046 (2)*0.1254 (10)
H14B0.33820.98090.89910.055*0.1254 (10)
C15A0.1817 (14)0.8754 (18)0.8305 (9)0.048 (5)*0.1254 (10)
C16A0.1241 (9)0.7972 (10)0.7680 (6)0.027 (2)*0.1254 (10)
C17A0.1716 (10)0.7720 (12)0.7287 (7)0.048 (2)*0.1254 (10)
H17B0.13180.72110.68600.058*0.1254 (10)
C18A0.2820 (9)0.8227 (10)0.7524 (6)0.041 (2)*0.1254 (10)
C19A0.4243 (10)0.8301 (12)0.7212 (7)0.035 (3)*0.1254 (10)
C20A0.5847 (8)1.0206 (11)0.7164 (6)0.033 (2)*0.1254 (10)
C21A0.6731 (9)1.0117 (10)0.7060 (5)0.0286 (19)*0.1254 (10)
H21B0.74130.97320.74480.034*0.1254 (10)
C22A0.5769 (8)1.1114 (9)0.5894 (5)0.024 (2)*0.1254 (10)
C23A0.5778 (9)1.1551 (10)0.5272 (6)0.0317 (19)*0.1254 (10)
H23B0.64321.14360.52470.038*0.1254 (10)
C24A0.4813 (10)1.2138 (10)0.4716 (6)0.031 (2)*0.1254 (10)
H24B0.47971.24450.43000.037*0.1254 (10)
C25A0.3878 (9)1.2287 (11)0.4753 (6)0.034 (2)*0.1254 (10)
H25B0.32171.26790.43520.041*0.1254 (10)
C26A0.3840 (8)1.1899 (9)0.5342 (5)0.0336 (18)*0.1254 (10)
H26B0.31761.20410.53510.040*0.1254 (10)
C27A0.4813 (8)1.1283 (8)0.5935 (5)0.0260 (16)*0.1254 (10)
C28A0.4785 (7)1.0841 (8)0.6611 (4)0.0280 (16)*0.1254 (10)
C29A1.1849 (10)0.5735 (12)1.0420 (6)0.045 (2)*0.1254 (10)
H29D1.18010.48301.03980.068*0.1254 (10)
H29E1.20750.60151.09130.068*0.1254 (10)
H29F1.24240.60091.03220.068*0.1254 (10)
C30A1.0507 (12)0.4649 (12)0.8946 (8)0.049 (3)*0.1254 (10)
H30D0.99840.43970.84290.074*0.1254 (10)
H30E1.05950.39670.92710.074*0.1254 (10)
H30F1.12600.48590.90380.074*0.1254 (10)
C31A0.1392 (18)0.918 (2)0.8814 (12)0.069 (3)*0.1254 (10)
H31D0.05890.94520.85040.103*0.1254 (10)
H31E0.18740.98620.91310.103*0.1254 (10)
H31F0.14500.84820.91230.103*0.1254 (10)
C32A0.0079 (13)0.7464 (19)0.7496 (11)0.069 (3)*0.1254 (10)
H32D−0.01980.68320.71090.103*0.1254 (10)
H32E−0.04820.81400.73200.103*0.1254 (10)
H32F0.01770.70960.79410.103*0.1254 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C100.0265 (4)0.0190 (4)0.0206 (4)−0.0010 (3)0.0121 (3)−0.0029 (3)
O10.0225 (3)0.0216 (3)0.0249 (4)0.0024 (3)0.0124 (3)−0.0007 (3)
O20.0399 (5)0.0251 (4)0.0264 (4)0.0006 (3)0.0226 (4)−0.0008 (3)
O30.0280 (4)0.0259 (4)0.0247 (4)0.0035 (3)0.0148 (3)0.0055 (3)
O40.0241 (3)0.0214 (3)0.0183 (3)−0.0005 (3)0.0092 (3)−0.0027 (3)
O50.0281 (5)0.0508 (6)0.0222 (4)0.0020 (5)0.0075 (4)−0.0132 (4)
O60.0255 (5)0.0213 (4)0.0227 (4)−0.0005 (4)0.0127 (4)−0.0021 (3)
O70.0363 (5)0.0322 (4)0.0256 (4)−0.0021 (4)0.0160 (4)−0.0099 (3)
O80.0274 (5)0.0360 (5)0.0387 (5)0.0038 (4)0.0195 (4)0.0097 (4)
C10.0222 (5)0.0185 (5)0.0200 (5)0.0017 (4)0.0120 (4)0.0006 (4)
C20.0212 (5)0.0253 (5)0.0264 (5)0.0021 (4)0.0141 (4)0.0057 (4)
C30.0252 (5)0.0252 (5)0.0420 (7)0.0033 (4)0.0200 (5)0.0071 (5)
C40.0227 (5)0.0330 (6)0.0440 (7)0.0055 (5)0.0193 (5)0.0176 (5)
C50.0220 (6)0.0513 (9)0.0322 (7)0.0034 (6)0.0143 (5)0.0169 (7)
C60.0239 (5)0.0516 (8)0.0214 (5)0.0034 (5)0.0105 (4)0.0078 (5)
C70.0230 (5)0.0330 (6)0.0187 (5)0.0021 (5)0.0109 (4)0.0027 (5)
C80.0237 (5)0.0328 (5)0.0179 (4)−0.0009 (4)0.0100 (4)−0.0028 (4)
C90.0226 (4)0.0215 (4)0.0166 (4)−0.0008 (4)0.0092 (4)−0.0019 (3)
C110.0277 (5)0.0185 (4)0.0196 (4)0.0019 (4)0.0130 (4)−0.0002 (4)
C120.0262 (5)0.0176 (4)0.0204 (4)0.0027 (4)0.0126 (4)0.0024 (3)
C130.0315 (6)0.0195 (5)0.0228 (6)0.0031 (4)0.0170 (5)0.0041 (5)
C140.0336 (6)0.0278 (5)0.0293 (5)0.0000 (5)0.0184 (5)0.0055 (4)
C150.0343 (8)0.0415 (8)0.0367 (8)−0.0054 (7)0.0208 (7)0.0075 (6)
C160.0487 (9)0.0403 (9)0.0430 (10)0.0034 (6)0.0350 (8)0.0108 (7)
C170.0514 (8)0.0311 (6)0.0366 (6)0.0029 (5)0.0331 (6)0.0051 (5)
C180.0370 (6)0.0225 (5)0.0282 (5)0.0031 (4)0.0216 (5)0.0056 (4)
C190.0320 (6)0.0211 (5)0.0239 (5)0.0022 (4)0.0167 (5)−0.0001 (4)
C200.0261 (6)0.0162 (4)0.0207 (5)−0.0018 (4)0.0135 (4)−0.0015 (3)
C210.0278 (5)0.0199 (4)0.0225 (5)0.0008 (4)0.0149 (4)0.0011 (4)
C220.0292 (5)0.0172 (4)0.0235 (5)−0.0019 (4)0.0148 (5)−0.0006 (4)
C230.0356 (6)0.0241 (5)0.0255 (6)−0.0017 (4)0.0168 (5)0.0017 (4)
C240.0425 (8)0.0246 (5)0.0265 (5)−0.0021 (5)0.0197 (6)0.0024 (4)
C250.0476 (8)0.0288 (6)0.0322 (6)−0.0037 (5)0.0279 (6)0.0014 (5)
C260.0361 (6)0.0256 (5)0.0320 (6)−0.0019 (5)0.0225 (5)−0.0005 (5)
C270.0295 (6)0.0175 (5)0.0251 (5)−0.0033 (4)0.0169 (5)−0.0016 (4)
C280.0267 (5)0.0191 (4)0.0260 (5)−0.0017 (4)0.0154 (4)−0.0004 (4)
C290.0316 (7)0.0426 (8)0.0702 (11)0.0122 (6)0.0260 (8)0.0186 (8)
C300.0261 (6)0.0766 (13)0.0359 (7)0.0093 (7)0.0112 (5)0.0214 (8)
C310.0491 (10)0.0669 (12)0.0586 (10)−0.0142 (9)0.0367 (9)0.0017 (9)
C320.0690 (14)0.0621 (13)0.0694 (13)−0.0066 (10)0.0575 (12)0.0031 (10)
Geometric parameters (Å, º) top
C10—C20A1.434 (10)C32—H32A0.9600
C10—C111.5069 (15)C32—H32B0.9600
C10—C91.5144 (14)C32—H32C0.9600
C10—C201.5355 (14)O1A—C1A1.334 (11)
C10—C9A1.594 (8)O1A—C2A1.410 (10)
C10—C11A1.631 (9)O2A—C19A1.356 (11)
C10—H10A0.9621O2A—C18A1.398 (11)
O1—C11.3626 (15)O3A—C21A1.342 (10)
O1—C21.3774 (14)O3A—C22A1.378 (10)
O2—C191.3612 (15)O4A—C1A1.224 (12)
O2—C181.3718 (16)O5A—C8A1.320 (9)
O3—C211.3489 (13)O5A—H5AA0.8200
O3—C221.3698 (14)O6A—C12A1.292 (10)
O4—C11.2270 (14)O6A—H6AB0.8200
O5—C81.3345 (15)O7A—C19A1.231 (11)
O5—H5A0.8200O8A—C28A1.254 (10)
O6—C121.3320 (13)C1A—C9A1.472 (12)
O6—H6B0.8200C2A—C7A1.378 (10)
O7—C191.2235 (16)C2A—C3A1.389 (11)
O8—C281.2309 (15)C3A—C4A1.390 (14)
C1—C91.4312 (16)C3A—H3AA0.9300
C2—C31.3865 (16)C4A—C5A1.408 (15)
C2—C71.3876 (18)C4A—C29A1.518 (14)
C3—C41.386 (2)C5A—C6A1.416 (14)
C3—H3A0.9300C5A—C30A1.482 (15)
C4—C51.411 (2)C6A—C7A1.338 (10)
C4—C291.514 (2)C6A—H6AA0.9300
C5—C61.390 (3)C7A—C8A1.459 (10)
C5—C301.498 (2)C8A—C9A1.324 (10)
C6—C71.4015 (17)C11A—C12A1.327 (10)
C6—H6A0.9300C11A—C19A1.436 (12)
C7—C81.4358 (17)C12A—C13A1.429 (11)
C8—C91.3651 (14)C13A—C14A1.383 (12)
C11—C121.3688 (16)C13A—C18A1.401 (11)
C11—C191.4435 (16)C14A—C15A1.485 (14)
C12—C131.4446 (17)C14A—H14B0.9300
C13—C141.3945 (19)C15A—C16A1.383 (13)
C13—C181.3962 (19)C15A—C31A1.548 (15)
C14—C151.387 (2)C16A—C17A1.336 (12)
C14—H14A0.9300C16A—C32A1.507 (14)
C15—C161.407 (3)C17A—C18A1.406 (12)
C15—C311.522 (3)C17A—H17B0.9300
C16—C171.371 (3)C20A—C21A1.344 (12)
C16—C321.509 (2)C20A—C28A1.432 (11)
C17—C181.3870 (18)C21A—H21B0.9300
C17—H17A0.9300C22A—C27A1.366 (11)
C20—C211.3472 (18)C22A—C23A1.406 (12)
C20—C281.4644 (16)C23A—C24A1.342 (12)
C21—H21A0.9300C23A—H23B0.9300
C22—C271.3823 (19)C24A—C25A1.330 (12)
C22—C231.3995 (18)C24A—H24B0.9300
C23—C241.3800 (19)C25A—C26A1.343 (12)
C23—H23A0.9300C25A—H25B0.9300
C24—C251.389 (2)C26A—C27A1.390 (11)
C24—H24A0.9300C26A—H26B0.9300
C25—C261.3828 (18)C27A—C28A1.530 (10)
C25—H25A0.9300C29A—H29D0.9600
C26—C271.4042 (18)C29A—H29E0.9600
C26—H26A0.9300C29A—H29F0.9600
C27—C281.4741 (16)C30A—H30D0.9600
C29—H29A0.9600C30A—H30E0.9600
C29—H29B0.9600C30A—H30F0.9600
C29—H29C0.9600C31A—H31D0.9600
C30—H30A0.9600C31A—H31E0.9600
C30—H30B0.9600C31A—H31F0.9600
C30—H30C0.9600C32A—H32D0.9600
C31—H31A0.9600C32A—H32E0.9600
C31—H31B0.9600C32A—H32F0.9600
C31—H31C0.9600
C20A—C10—C11134.2 (4)C8A—O5A—H5AA109.5
C20A—C10—C998.4 (4)C12A—O6A—H6AB109.5
C11—C10—C9112.09 (8)O4A—C1A—O1A118.8 (10)
C11—C10—C20114.64 (9)O4A—C1A—C9A124.4 (10)
C9—C10—C20114.40 (8)O1A—C1A—C9A116.5 (9)
C20A—C10—C9A118.3 (5)C7A—C2A—C3A120.7 (8)
C11—C10—C9A102.4 (3)C7A—C2A—O1A123.8 (8)
C20—C10—C9A136.9 (3)C3A—C2A—O1A115.6 (8)
C20A—C10—C11A117.7 (5)C2A—C3A—C4A118.0 (10)
C9—C10—C11A103.2 (3)C2A—C3A—H3AA121.0
C20—C10—C11A100.9 (3)C4A—C3A—H3AA121.0
C9A—C10—C11A104.4 (4)C3A—C4A—C5A121.7 (12)
C20A—C10—H10A99.2C3A—C4A—C29A119.0 (12)
C11—C10—H10A103.1C5A—C4A—C29A119.3 (12)
C9—C10—H10A107.0C4A—C5A—C6A117.4 (12)
C20—C10—H10A104.3C4A—C5A—C30A118.3 (12)
C9A—C10—H10A87.1C6A—C5A—C30A124.2 (13)
C11A—C10—H10A127.4C7A—C6A—C5A120.5 (9)
C1—O1—C2120.41 (9)C7A—C6A—H6AA119.7
C19—O2—C18121.04 (9)C5A—C6A—H6AA119.7
C21—O3—C22117.95 (10)C6A—C7A—C2A121.7 (7)
C8—O5—H5A109.5C6A—C7A—C8A124.3 (8)
C12—O6—H6B109.5C2A—C7A—C8A113.9 (7)
O4—C1—O1115.57 (10)O5A—C8A—C9A125.2 (8)
O4—C1—C9124.92 (12)O5A—C8A—C7A112.2 (7)
O1—C1—C9119.51 (10)C9A—C8A—C7A122.6 (7)
O1—C2—C3116.57 (11)C8A—C9A—C1A121.4 (8)
O1—C2—C7121.53 (10)C8A—C9A—C10124.2 (7)
C3—C2—C7121.88 (11)C1A—C9A—C10114.1 (7)
C4—C3—C2119.20 (14)C12A—C11A—C19A122.1 (8)
C4—C3—H3A120.4C12A—C11A—C10123.4 (7)
C2—C3—H3A120.4C19A—C11A—C10114.4 (7)
C3—C4—C5120.82 (15)O6A—C12A—C11A127.8 (9)
C3—C4—C29119.16 (17)O6A—C12A—C13A111.0 (8)
C5—C4—C29120.01 (16)C11A—C12A—C13A121.2 (8)
C6—C5—C4118.28 (14)C14A—C13A—C18A117.6 (9)
C6—C5—C30120.05 (18)C14A—C13A—C12A127.1 (9)
C4—C5—C30121.66 (19)C18A—C13A—C12A115.1 (8)
C5—C6—C7121.72 (14)C13A—C14A—C15A117.9 (10)
C5—C6—H6A119.1C13A—C14A—H14B121.1
C7—C6—H6A119.1C15A—C14A—H14B121.1
C2—C7—C6118.09 (12)C16A—C15A—C14A120.9 (11)
C2—C7—C8118.20 (11)C16A—C15A—C31A127.6 (13)
C6—C7—C8123.69 (14)C14A—C15A—C31A111.5 (12)
O5—C8—C9124.82 (11)C17A—C16A—C15A120.3 (10)
O5—C8—C7115.36 (11)C17A—C16A—C32A124.7 (11)
C9—C8—C7119.81 (11)C15A—C16A—C32A115.0 (11)
C8—C9—C1119.81 (11)C16A—C17A—C18A119.6 (10)
C8—C9—C10121.20 (10)C16A—C17A—H17B120.2
C1—C9—C10118.95 (9)C18A—C17A—H17B120.2
C12—C11—C19119.07 (11)O2A—C18A—C13A123.7 (8)
C12—C11—C10125.27 (9)O2A—C18A—C17A112.6 (8)
C19—C11—C10115.44 (10)C13A—C18A—C17A123.7 (9)
O6—C12—C11124.86 (11)O7A—C19A—O2A116.3 (9)
O6—C12—C13114.82 (11)O7A—C19A—C11A125.3 (9)
C11—C12—C13120.27 (11)O2A—C19A—C11A118.3 (9)
C14—C13—C18118.25 (12)C21A—C20A—C28A119.5 (9)
C14—C13—C12124.36 (14)C21A—C20A—C10121.8 (8)
C18—C13—C12117.38 (12)C28A—C20A—C10118.1 (7)
C15—C14—C13120.78 (14)O3A—C21A—C20A128.4 (9)
C15—C14—H14A119.6O3A—C21A—H21B115.8
C13—C14—H14A119.6C20A—C21A—H21B115.8
C14—C15—C16119.57 (16)C27A—C22A—O3A120.5 (8)
C14—C15—C31118.35 (16)C27A—C22A—C23A121.4 (8)
C16—C15—C31122.05 (15)O3A—C22A—C23A118.1 (8)
C17—C16—C15120.19 (16)C24A—C23A—C22A117.8 (9)
C17—C16—C32120.3 (2)C24A—C23A—H23B121.1
C15—C16—C32119.47 (19)C22A—C23A—H23B121.1
C16—C17—C18119.65 (15)C25A—C24A—C23A120.6 (9)
C16—C17—H17A120.2C25A—C24A—H24B119.7
C18—C17—H17A120.2C23A—C24A—H24B119.7
O2—C18—C17116.80 (11)C24A—C25A—C26A123.4 (10)
O2—C18—C13121.68 (11)C24A—C25A—H25B118.3
C17—C18—C13121.49 (13)C26A—C25A—H25B118.3
O7—C19—O2116.02 (10)C25A—C26A—C27A118.7 (9)
O7—C19—C11124.61 (13)C25A—C26A—H26B120.7
O2—C19—C11119.35 (11)C27A—C26A—H26B120.7
C21—C20—C28118.97 (10)C22A—C27A—C26A118.1 (8)
C21—C20—C10121.06 (10)C22A—C27A—C28A122.6 (8)
C28—C20—C10119.56 (11)C26A—C27A—C28A119.3 (8)
C20—C21—O3126.09 (11)O8A—C28A—C20A124.8 (8)
C20—C21—H21A117.0O8A—C28A—C27A123.3 (7)
O3—C21—H21A117.0C20A—C28A—C27A111.9 (7)
O3—C22—C27121.94 (11)C4A—C29A—H29D109.5
O3—C22—C23115.90 (12)C4A—C29A—H29E109.5
C27—C22—C23122.16 (12)H29D—C29A—H29E109.5
C24—C23—C22118.10 (13)C4A—C29A—H29F109.5
C24—C23—H23A121.0H29D—C29A—H29F109.5
C22—C23—H23A121.0H29E—C29A—H29F109.5
C23—C24—C25121.06 (12)C5A—C30A—H30D109.5
C23—C24—H24A119.5C5A—C30A—H30E109.5
C25—C24—H24A119.5H30D—C30A—H30E109.5
C26—C25—C24120.13 (12)C5A—C30A—H30F109.5
C26—C25—H25A119.9H30D—C30A—H30F109.5
C24—C25—H25A119.9H30E—C30A—H30F109.5
C25—C26—C27120.16 (13)C15A—C31A—H31D109.5
C25—C26—H26A119.9C15A—C31A—H31E109.5
C27—C26—H26A119.9H31D—C31A—H31E109.5
C22—C27—C26118.39 (11)C15A—C31A—H31F109.5
C22—C27—C28120.52 (12)H31D—C31A—H31F109.5
C26—C27—C28121.09 (13)H31E—C31A—H31F109.5
O8—C28—C20122.95 (11)C16A—C32A—H32D109.5
O8—C28—C27122.52 (11)C16A—C32A—H32E109.5
C20—C28—C27114.52 (11)H32D—C32A—H32E109.5
C1A—O1A—C2A121.8 (8)C16A—C32A—H32F109.5
C19A—O2A—C18A119.1 (8)H32D—C32A—H32F109.5
C21A—O3A—C22A116.9 (8)H32E—C32A—H32F109.5
C2—O1—C1—O4−171.66 (9)C2A—O1A—C1A—O4A172.7 (7)
C2—O1—C1—C98.03 (15)C2A—O1A—C1A—C9A−1.2 (2)
C1—O1—C2—C3177.31 (10)C1A—O1A—C2A—C7A−0.4 (3)
C1—O1—C2—C7−1.20 (16)C1A—O1A—C2A—C3A179.6 (3)
O1—C2—C3—C4−177.41 (10)C7A—C2A—C3A—C4A−0.2 (7)
C7—C2—C3—C41.09 (18)O1A—C2A—C3A—C4A179.8 (4)
C2—C3—C4—C5−1.08 (19)C2A—C3A—C4A—C5A0.5 (8)
C2—C3—C4—C29−179.88 (12)C2A—C3A—C4A—C29A178.4 (8)
C3—C4—C5—C60.3 (2)C3A—C4A—C5A—C6A−0.8 (9)
C29—C4—C5—C6179.14 (14)C29A—C4A—C5A—C6A−178.7 (9)
C3—C4—C5—C30−178.39 (14)C3A—C4A—C5A—C30A−179.5 (10)
C29—C4—C5—C300.4 (2)C29A—C4A—C5A—C30A2.6 (12)
C4—C5—C6—C70.4 (2)C4A—C5A—C6A—C7A0.9 (8)
C30—C5—C6—C7179.16 (13)C30A—C5A—C6A—C7A179.5 (10)
O1—C2—C7—C6178.06 (11)C5A—C6A—C7A—C2A−0.6 (8)
C3—C2—C7—C6−0.36 (18)C5A—C6A—C7A—C8A179.2 (5)
O1—C2—C7—C8−3.57 (17)C3A—C2A—C7A—C6A0.3 (6)
C3—C2—C7—C8178.00 (11)O1A—C2A—C7A—C6A−179.8 (4)
C5—C6—C7—C2−0.4 (2)C3A—C2A—C7A—C8A−179.6 (4)
C5—C6—C7—C8−178.66 (13)O1A—C2A—C7A—C8A0.4 (5)
C2—C7—C8—O5−177.72 (11)C6A—C7A—C8A—O5A2.7 (8)
C6—C7—C8—O50.55 (18)C2A—C7A—C8A—O5A−177.5 (6)
C2—C7—C8—C91.32 (17)C6A—C7A—C8A—C9A−178.4 (5)
C6—C7—C8—C9179.59 (12)C2A—C7A—C8A—C9A1.4 (7)
O5—C8—C9—C1−175.66 (12)O5A—C8A—C9A—C1A175.6 (6)
C7—C8—C9—C15.39 (17)C7A—C8A—C9A—C1A−3.1 (8)
O5—C8—C9—C101.90 (18)O5A—C8A—C9A—C10−10.5 (9)
C7—C8—C9—C10−177.05 (10)C7A—C8A—C9A—C10170.8 (5)
O4—C1—C9—C8169.48 (11)O4A—C1A—C9A—C8A−170.6 (8)
O1—C1—C9—C8−10.18 (16)O1A—C1A—C9A—C8A3.0 (6)
O4—C1—C9—C10−8.13 (17)O4A—C1A—C9A—C1015.0 (8)
O1—C1—C9—C10172.21 (9)O1A—C1A—C9A—C10−171.5 (4)
C20A—C10—C9—C8128.7 (5)C20A—C10—C9A—C8A−45.1 (8)
C11—C10—C9—C8−86.11 (12)C11—C10—C9A—C8A113.1 (5)
C20—C10—C9—C8141.18 (11)C9—C10—C9A—C8A−2.5 (4)
C9A—C10—C9—C8−14.2 (6)C20—C10—C9A—C8A−36.2 (7)
C11A—C10—C9—C8−110.2 (3)C11A—C10—C9A—C8A88.0 (6)
C20A—C10—C9—C1−53.7 (5)C20A—C10—C9A—C1A129.2 (6)
C11—C10—C9—C191.47 (11)C11—C10—C9A—C1A−72.6 (4)
C20—C10—C9—C1−41.24 (13)C9—C10—C9A—C1A171.8 (8)
C9A—C10—C9—C1163.3 (6)C20—C10—C9A—C1A138.1 (4)
C11A—C10—C9—C167.4 (3)C11A—C10—C9A—C1A−97.7 (5)
C20A—C10—C11—C1250.1 (7)C20A—C10—C11A—C12A−137.7 (9)
C9—C10—C11—C12−77.94 (13)C11—C10—C11A—C12A0.6 (5)
C20—C10—C11—C1254.65 (13)C9—C10—C11A—C12A115.2 (8)
C9A—C10—C11—C12−102.8 (3)C20—C10—C11A—C12A−126.3 (8)
C11A—C10—C11—C12−5.1 (7)C9A—C10—C11A—C12A88.9 (9)
C20A—C10—C11—C19−135.3 (6)C20A—C10—C11A—C19A39.3 (10)
C9—C10—C11—C1996.63 (11)C11—C10—C11A—C19A177.6 (14)
C20—C10—C11—C19−130.78 (10)C9—C10—C11A—C19A−67.8 (8)
C9A—C10—C11—C1971.8 (3)C20—C10—C11A—C19A50.7 (8)
C11A—C10—C11—C19169.4 (8)C9A—C10—C11A—C19A−94.1 (9)
C19—C11—C12—O6−171.62 (10)C19A—C11A—C12A—O6A172.9 (11)
C10—C11—C12—O62.77 (17)C10—C11A—C12A—O6A−10.3 (16)
C19—C11—C12—C1311.37 (15)C19A—C11A—C12A—C13A−6.7 (16)
C10—C11—C12—C13−174.24 (10)C10—C11A—C12A—C13A170.1 (8)
O6—C12—C13—C14−1.77 (17)O6A—C12A—C13A—C14A5.4 (17)
C11—C12—C13—C14175.53 (11)C11A—C12A—C13A—C14A−174.9 (11)
O6—C12—C13—C18179.45 (10)O6A—C12A—C13A—C18A−178.5 (10)
C11—C12—C13—C18−3.26 (16)C11A—C12A—C13A—C18A1.2 (16)
C18—C13—C14—C151.59 (19)C18A—C13A—C14A—C15A0.7 (19)
C12—C13—C14—C15−177.19 (12)C12A—C13A—C14A—C15A176.7 (14)
C13—C14—C15—C160.9 (2)C13A—C14A—C15A—C16A1 (2)
C13—C14—C15—C31−176.94 (14)C13A—C14A—C15A—C31A−179.5 (15)
C14—C15—C16—C17−2.6 (3)C14A—C15A—C16A—C17A−2 (3)
C31—C15—C16—C17175.13 (17)C31A—C15A—C16A—C17A178.3 (18)
C14—C15—C16—C32178.38 (17)C14A—C15A—C16A—C32A178.1 (15)
C31—C15—C16—C32−3.9 (3)C31A—C15A—C16A—C32A−1 (3)
C15—C16—C17—C181.8 (2)C15A—C16A—C17A—C18A2 (2)
C32—C16—C17—C18−179.22 (16)C32A—C16A—C17A—C18A−178.6 (13)
C19—O2—C18—C17−176.24 (11)C19A—O2A—C18A—C13A−5.1 (16)
C19—O2—C18—C135.45 (16)C19A—O2A—C18A—C17A177.1 (11)
C16—C17—C18—O2−177.54 (14)C14A—C13A—C18A—O2A−178.7 (10)
C16—C17—C18—C130.8 (2)C12A—C13A—C18A—O2A4.7 (16)
C14—C13—C18—O2175.78 (11)C14A—C13A—C18A—C17A−1.2 (18)
C12—C13—C18—O2−5.36 (17)C12A—C13A—C18A—C17A−177.7 (11)
C14—C13—C18—C17−2.45 (18)C16A—C17A—C18A—O2A177.8 (10)
C12—C13—C18—C17176.41 (11)C16A—C17A—C18A—C13A0.0 (19)
C18—O2—C19—O7−175.43 (10)C18A—O2A—C19A—O7A176.3 (10)
C18—O2—C19—C112.96 (15)C18A—O2A—C19A—C11A−0.4 (16)
C12—C11—C19—O7166.87 (11)C12A—C11A—C19A—O7A−170.1 (12)
C10—C11—C19—O7−8.06 (16)C10—C11A—C19A—O7A12.9 (17)
C12—C11—C19—O2−11.37 (16)C12A—C11A—C19A—O2A6.3 (17)
C10—C11—C19—O2173.71 (9)C10—C11A—C19A—O2A−170.7 (9)
C20A—C10—C20—C21−176.1 (14)C11—C10—C20A—C21A−166.5 (7)
C11—C10—C20—C2113.43 (14)C9—C10—C20A—C21A−34.0 (11)
C9—C10—C20—C21144.92 (10)C20—C10—C20A—C21A−179 (2)
C9A—C10—C20—C21160.2 (4)C9A—C10—C20A—C21A−16.8 (13)
C11A—C10—C20—C2134.9 (3)C11A—C10—C20A—C21A−143.8 (9)
C20A—C10—C20—C28−3.5 (14)C11—C10—C20A—C28A22.7 (13)
C11—C10—C20—C28−173.96 (9)C9—C10—C20A—C28A155.2 (8)
C9—C10—C20—C28−42.48 (13)C20—C10—C20A—C28A10.5 (7)
C9A—C10—C20—C28−27.2 (4)C9A—C10—C20A—C28A172.3 (7)
C11A—C10—C20—C28−152.5 (3)C11A—C10—C20A—C28A45.3 (11)
C28—C20—C21—O30.20 (17)C22A—O3A—C21A—C20A1.7 (16)
C10—C20—C21—O3172.84 (10)C28A—C20A—C21A—O3A−3.0 (18)
C22—O3—C21—C20−0.82 (17)C10—C20A—C21A—O3A−173.7 (9)
C21—O3—C22—C271.23 (15)C21A—O3A—C22A—C27A−0.5 (13)
C21—O3—C22—C23−178.99 (10)C21A—O3A—C22A—C23A179.2 (9)
O3—C22—C23—C24−179.25 (11)C27A—C22A—C23A—C24A−0.2 (15)
C27—C22—C23—C240.53 (17)O3A—C22A—C23A—C24A−179.9 (9)
C22—C23—C24—C25−0.91 (19)C22A—C23A—C24A—C25A−0.7 (16)
C23—C24—C25—C260.6 (2)C23A—C24A—C25A—C26A1.6 (18)
C24—C25—C26—C270.06 (19)C24A—C25A—C26A—C27A−1.7 (17)
O3—C22—C27—C26179.91 (10)O3A—C22A—C27A—C26A179.9 (9)
C23—C22—C27—C260.14 (17)C23A—C22A—C27A—C26A0.1 (14)
O3—C22—C27—C28−1.03 (16)O3A—C22A—C27A—C28A0.9 (14)
C23—C22—C27—C28179.20 (11)C23A—C22A—C27A—C28A−178.8 (9)
C25—C26—C27—C22−0.44 (18)C25A—C26A—C27A—C22A0.8 (14)
C25—C26—C27—C28−179.50 (11)C25A—C26A—C27A—C28A179.7 (9)
C21—C20—C28—O8178.56 (11)C21A—C20A—C28A—O8A−177.6 (10)
C10—C20—C28—O85.80 (16)C10—C20A—C28A—O8A−6.6 (15)
C21—C20—C28—C270.04 (15)C21A—C20A—C28A—C27A2.9 (14)
C10—C20—C28—C27−172.72 (9)C10—C20A—C28A—C27A173.9 (8)
C22—C27—C28—O8−178.16 (11)C22A—C27A—C28A—O8A178.4 (9)
C26—C27—C28—O80.88 (18)C26A—C27A—C28A—O8A−0.5 (14)
C22—C27—C28—C200.37 (15)C22A—C27A—C28A—C20A−2.1 (13)
C26—C27—C28—C20179.41 (10)C26A—C27A—C28A—C20A179.0 (9)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C2–C7 and C2A–C7A benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
O5—H5A···O70.821.832.6464 (19)174
O6—H6B···O40.821.802.6141 (18)172
C3—H3A···Cg1i0.932.913.7691 (16)155
C32—H32B···Cg2ii0.962.703.499 (3)140
C29A—H29D···Cg3iii0.962.913.591 (15)128
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC32H24O8
Mr536.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.6418 (12), 10.5878 (9), 21.2316 (15)
β (°) 123.480 (4)
V (Å3)2557.8 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.56 × 0.30 × 0.28
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.946, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections		37636, 10128, 7464
Rint0.037
(sin θ/λ)max (Å−1)0.782
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.141, 1.03
No. of reflections10128
No. of parameters524
No. of restraints1102
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C2–C7 and C2A–C7A benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
O5—H5A···O70.821.832.6464 (19)174
O6—H6B···O40.821.802.6141 (18)172
C3—H3A···Cg1i0.932.913.7691 (16)155
C32—H32B···Cg2ii0.962.703.499 (3)140
C29A—H29D···Cg3iii0.962.913.591 (15)128
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+2.
 

Footnotes

‡Additional correspondence author, e-mail: oocw@usm.my.

§Thomson Reuters ResearcherID: A-5523-2009.

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors are thankful to Universiti Sains Malaysia (USM) for providing the necessary research facilities and RU research funding under grant No. 1001/PKIMIA/811134. MA also thanks USM for the award of post doctoral fellowship. HKF and CSY thank USM for the Research University Grant No. 1001/PFIZIK/811160.

References

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2859-o2860
https://doi.org/10.1107/S1600536810041231
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